diff --git a/src/business/business-gnome/dialog-payment.c b/src/business/business-gnome/dialog-payment.c
index 11b0c3ee9e..96d20e4a42 100644
--- a/src/business/business-gnome/dialog-payment.c
+++ b/src/business/business-gnome/dialog-payment.c
@@ -1170,19 +1170,34 @@ gnc_ui_payment_new (GncOwner *owner, QofBook *book)
 gboolean gnc_ui_payment_is_customer_payment(const Transaction *txn)
 {
     gboolean result = TRUE;
-    Split *assetaccount_split;
+    Split *assetaccount_split, *aparaccount_split;
     gnc_numeric amount;
 
     if (!txn)
         return result;
 
-    // We require the txn to have one split in an A/R or A/P account.
-
     if (!xaccTransGetSplitList(txn))
         return result;
+
+    /* First test if one split is in an A/R or A/P account.
+     * That will give us the best Customer vs Vendor/Employee distinction */
+    aparaccount_split = xaccTransGetFirstAPARAcctSplit(txn);
+    if (aparaccount_split)
+    {
+        if (xaccAccountGetType (xaccSplitGetAccount (aparaccount_split)) == ACCT_TYPE_RECEIVABLE)
+            return TRUE;  // Type is Customer
+        else if (xaccAccountGetType (xaccSplitGetAccount (aparaccount_split)) == ACCT_TYPE_PAYABLE)
+            return FALSE; // Type is Vendor/Employee, there's not enough information to refine more
+    }
+
+    /* For the lack of an A/R or A/P account we'll assume positive changes to an
+     * Asset/Liability or Equity account are Customer payments the others will be
+     * considered Vendor payments */
     assetaccount_split = xaccTransGetFirstPaymentAcctSplit(txn);
     if (!assetaccount_split)
     {
+        /* Transaction isn't valid for a payment, just return the default
+         * Calling code will have to handle this situation properly */
         g_message("No asset splits in txn \"%s\"; cannot use this for assigning a payment.",
                   xaccTransGetDescription(txn));
         return result;
diff --git a/src/business/business-gnome/gnc-plugin-business.c b/src/business/business-gnome/gnc-plugin-business.c
index 2c493f863a..b82a747214 100644
--- a/src/business/business-gnome/gnc-plugin-business.c
+++ b/src/business/business-gnome/gnc-plugin-business.c
@@ -822,7 +822,9 @@ static void gnc_plugin_business_cmd_assign_payment (GtkAction *action,
     SplitRegister *reg;
     Split *split;
     Transaction *trans;
-    gboolean is_customer;
+    gboolean have_owner;
+    GncOwner owner;
+    GncOwner *owner_p;
 
     g_return_if_fail (mw != NULL);
     g_return_if_fail (GNC_IS_PLUGIN_BUSINESS (mw->data));
@@ -846,16 +848,20 @@ static void gnc_plugin_business_cmd_assign_payment (GtkAction *action,
 
     trans = xaccSplitGetParent(split);
     g_return_if_fail(trans);
-    is_customer = gnc_ui_payment_is_customer_payment(trans);
 
     plugin_business = GNC_PLUGIN_BUSINESS (mw->data);
     plugin_business_priv = GNC_PLUGIN_BUSINESS_GET_PRIVATE (plugin_business);
 
+    have_owner = gncOwnerGetOwnerFromTxn (trans, &owner);
+    if (have_owner)
+        owner_p = &owner;
+    else if (gnc_ui_payment_is_customer_payment(trans))
+        owner_p = plugin_business_priv->last_customer;
+    else
+        owner_p = plugin_business_priv->last_vendor;
+
     gnc_business_assign_payment (gnc_plugin_page_get_window(plugin_page),
-                                 trans,
-                                 is_customer
-                                 ? plugin_business_priv->last_customer
-                                 : plugin_business_priv->last_vendor);
+                                 trans, owner_p);
 }
 
 static const gchar *register_txn_actions[] =